EP3000866A1 - Schmiermittelzusammensetzung - Google Patents

Schmiermittelzusammensetzung Download PDF

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Publication number
EP3000866A1
EP3000866A1 EP14801604.1A EP14801604A EP3000866A1 EP 3000866 A1 EP3000866 A1 EP 3000866A1 EP 14801604 A EP14801604 A EP 14801604A EP 3000866 A1 EP3000866 A1 EP 3000866A1
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EP
European Patent Office
Prior art keywords
mass
lubricating oil
less
oil composition
basis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP14801604.1A
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English (en)
French (fr)
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EP3000866A4 (de
Inventor
Junya Iwasaki
Yasunori Shimizu
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Publication of EP3000866A1 publication Critical patent/EP3000866A1/de
Publication of EP3000866A4 publication Critical patent/EP3000866A4/de
Withdrawn legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02Petroleum fractions
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68Esters
    • C10M129/70Esters of monocarboxylic acids
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68Esters
    • C10M129/72Esters of polycarboxylic acids
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38Heterocyclic nitrogen compounds
    • C10M133/40Six-membered ring containing nitrogen and carbon only
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102Aliphatic fractions
    • C10M2203/1025Aliphatic fractions used as base material
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028Overbased salts thereof
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/289Partial esters containing free hydroxy groups
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/223Five-membered rings containing nitrogen and carbon only
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28Amides; Imides
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
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    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02Unspecified siloxanes; Silicones
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04Detergent property or dispersant property
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08Resistance to extreme temperature
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10Inhibition of oxidation, e.g. anti-oxidants
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/40Low content or no content compositions
    • C10N2030/42Phosphor free or low phosphor content compositions
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/40Low content or no content compositions
    • C10N2030/45Ash-less or low ash content
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/52Base number [TBN]
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/252Diesel engines
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2060/00Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/14Chemical after-treatment of the constituents of the lubricating composition by boron or a compound containing boron

Definitions

  • the present invention relates to a lubricating oil composition and also relates to a lubricating oil composition for internal combustion engines.
  • a method of reducing the ash there is exemplified a method of reducing the amount of a metallic detergent.
  • the metallic detergent was essential from the viewpoint of improving the acid neutralizing properties, and hence, if the addition amount of the metallic detergent is reduced for the purpose of reducing the ash, there is a concern that detergency of the lubricating oil composition is lowered.
  • the addition amount of the metallic detergent is reduced, the acid neutralizing properties are lowered, and hence, there is also a concern that oxidation deterioration of the lubricating oil composition is liable to progress.
  • Patent Document 1 there has been proposed a so-called ash-free detergent-dispersant as a replacement of the metallic detergent.
  • Patent Document 2 there has been proposed addition of a specified heterocyclic compound capable of preventing oxidation deterioration of the lubricating oil composition from occurring (see Patent Document 2).
  • an object of the present invention is to provide a lubricating oil composition capable of maintaining high-temperature detergency and acid neutralizing properties, even when amounts of a phosphorus component-containing additive and a metallic detergent are reduced.
  • the present inventors made extensive and intensive investigations. As a result, it has been found that the object can be achieved by a lubricating oil composition comprising a substituted hydroxy aromatic carboxylic acid ester derivative and a specified heterocyclic compound blended therein.
  • the present invention has been accomplished on the basis of such finding. Specifically, the present invention provides the following:
  • the present invention provides the lubricating oil composition as set forth in any one of the above items [1] to [6], wherein, in the general formula (III) or (IV), R 4 is a hydrogen atom or a methyl group, or the lubricating oil composition as set forth in any one of the above items [1] to [6], wherein, in the general formula (III) or (IV), R 4 is a hydrogen atom.
  • the present invention provides a lubricating oil composition containing a base oil, (A) a substituted hydroxy aromatic carboxylic acid ester derivative represented by at least one of the general formula (I) and the general formula (II), and (B) a heterocyclic compound represented by the general formula (III) or (IV), wherein a phosphorus content is 0.06 mass% or less on the basis of a total amount of the composition, and a sulfated ash content is 1.2 mass% or less on the basis of a total amount of the composition.
  • the present invention provides a method for producing a lubricating oil composition, which includes blending a base oil, (A) a substituted hydroxy aromatic carboxylic acid ester derivative represented by at least one of the general formula (I) and the general formula (II), and (B) a heterocyclic compound represented by the general formula (III) or (IV), thereby producing a lubricating oil composition having a phosphorus content of 0.06 mass% or less on the basis of a total amount of the composition and a sulfated ash content of 1.2 mass% or less on the basis of a total amount of the composition.
  • a lubricating oil composition capable of maintaining high-temperature detergency and acid neutralizing properties, even when amounts of a phosphorus component-containing additive and a metallic detergent are reduced.
  • a lubricating oil composition includes a base oil, (A) a substituted hydroxy aromatic carboxylic acid ester derivative represented by at least one of the general formula (I) and the general formula (II), and (B) a heterocyclic compound represented by the general formula (III) or (IV) blended therein, wherein a phosphorus content is 0.06 mass% or less on the basis of a total amount of the composition, and a sulfated ash content is 1.2 mass% or less on the basis of a total amount of the composition.
  • each of x and y is an integer satisfying 1 ⁇ x ⁇ 3 and 1 ⁇ y ⁇ 3, respectively; each of R 1 and R 2 represents an alkyl group having 9 to 20 carbon atoms and may be the same as or different from each other; and in the case of 2 ⁇ x ⁇ 3 and 2 ⁇ y ⁇ 3, plural R 1 s may be the same as or different from each other and plural R 2 s may be the same as or different from each other.
  • each of m, n, o, and p is an integer satisfying 1 ⁇ m ⁇ 2, 0 ⁇ n ⁇ 2, 2 ⁇ (m + n) ⁇ 4, 1 ⁇ o ⁇ 3, and 1 ⁇ p ⁇ 3, respectively; each of R 1 and R 2 represents an alkyl group having 9 to 20 carbon atoms and may be the same as or different from each other; and in the case of 2 ⁇ o ⁇ 3 and 2 ⁇ p ⁇ 3, plural R 1 s may be the same as or different from each other and plural R 2 s may be the same as or different from each other. or
  • R 3 represents a linear or branched alkyl group having 7 to 17 carbon atoms; n is 6 to 18; in the case where a plurality of R 4 s are present, each R 4 is independently a group selected from a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a -COR 5 group, and an -OR 6 group; R 5 is an alkyl group having 1 to 17 carbon atoms; and R 6 is an alkyl group having 1 to 18 carbon atoms.
  • the lubricating oil composition containing a base oil, (A) a substituted hydroxy aromatic carboxylic acid ester derivative represented by at least one of the general formula (I) and the general formula (II), and (B) a heterocyclic compound represented by the general formula (III) or (IV) blended therein is one generally containing those blended compounds.
  • at least a part of the compounds contained in the lubricating oil composition may be converted to a different compound upon reaction.
  • any arbitrary oils including mineral oils and synthetic oils which have hitherto been used as a base oil of lubricating oils may be properly selected and used.
  • the type of the mineral oil and the synthetic oil is not specifically limited, and for use herein, any one may be suitably selected from the group consisting of a mineral oil and a synthetic oil heretofore used as the base oil in lubricating oil.
  • Examples of the mineral oil include a mineral oil refined by subjecting a lubricating oil distillate that is obtained by distilling under a reduced pressure the atmospheric residue given by atmospheric distillation of crude oil, to one or more treatments selected from the group consisting of solvent deasphalting, solvent extraction, hydro-cracking, solvent dewaxing, catalytic dewaxing, hydrorefining and the like, and a mineral oil produced by isomerization of wax or GTL WAX and the like.
  • examples of the synthetic oil include polybutene, polyolefins [ ⁇ -olefin homopolymers and copolymers (e.g., ethylene- ⁇ -olefin copolymers)], various kinds of esters (for example, polyol esters, dibasic acid esters, phosphate esters), various kinds of ethers (for example, polyphenyl ethers), polyglycols, alkylbenzenes, alkylnaphthalenes, etc.
  • esters for example, polyol esters, dibasic acid esters, phosphate esters
  • ethers for example, polyphenyl ethers
  • polyglycols for example, polyphenyl ethers
  • alkylbenzenes alkylnaphthalenes
  • alkylnaphthalenes etc.
  • synthetic oils polyolefins and polyol esters are particularly preferred.
  • the aforementioned mineral oils may be used alone or in combinations of two or more thereof.
  • the aforementioned synthetic oils may be used alone or in combinations of two or more thereof.
  • one or more members of the mineral oils and one or more members of the synthetic oils may be used in combination.
  • a kinematic viscosity at 100°C of the base oil is preferably in the range of 1.5 mm 2 /s or more and 30 mm 2 /s or less, more preferably in the range of 3 mm 2 /s or more and 30 mm 2 /s or less, and still more preferably in the range of 3 mm 2 /s or more and 15 mm 2 /s or less. So long as the kinematic viscosity at 100°C is 1.5 mm 2 /s or more, a vaporization loss is suppressed, whereas so long as it is 30 mm 2 /s or less, a power loss attributable to viscous resistance is suppressed, so that a fuel consumption improvement effect is obtained.
  • a base oil having a %C A by ring analysis of 3.0 or less and a sulfur content of 50 ppm by mass or less is preferably used.
  • the "%C A by ring analysis” refers to an aromatic content (percentage) calculated by the ring analysis n-d-M method.
  • the sulfur content is a value measured in conformity with JIS K2541.
  • the base oil having a %C A of 3. 0 or less and a sulfur content of 50 ppm by mass or less can provide a lubricating oil composition having favorable oxidation stability and capable of suppressing an increase in acid number or sludge formation.
  • the %C A is more preferably 1.0 or less, and still more preferably 0.5 or less; and the sulfur content is more preferably 30 ppm by mass or less.
  • a viscosity index of the base oil is preferably 70 or more, more preferably 100 or more, and still more preferably 120 or more.
  • the base oil having a viscosity index of 70 or more is suppressed in terms of a variation in viscosity to be caused due to a change of temperature.
  • a pour point that is an index of low-temperature fluidity of this base oil is preferably -10°C or lower.
  • the substituted hydroxy aromatic carboxylic acid ester derivative which is used in the present invention is represented by the following general formula (I) or (II).
  • each of x and y is an integer satisfying 1 ⁇ x ⁇ 3 and 1 ⁇ y ⁇ 3, respectively; each of R 1 and R 2 represents an alkyl group having 9 to 20 carbon atoms and may be the same as or different from each other; and in the case of 2 ⁇ x ⁇ 3 and 2 ⁇ y ⁇ 3, plural R 1 s may be the same as or different from each other and plural R 2 s may be the same as or different from each other.
  • each of m, n, o, and p is an integer satisfying 1 ⁇ m ⁇ 2, 0 ⁇ n ⁇ 2, 2 ⁇ (m + n) ⁇ 4, 1 ⁇ o ⁇ 3, and 1 ⁇ p ⁇ 3, respectively; each of R 1 and R 2 represents an alkyl group having 9 to 20 carbon atoms and may be the same as or different from each other; and in the case of 2 ⁇ o ⁇ 3 and 2 ⁇ p ⁇ 3, plural R 1 s may be the same as or different from each other and plural R 2 s may be the same as or different from each other. More preferably, plural R 1 s are the same and plural R 2 s are the same.
  • examples of the alkyl group having 9 to 20 carbon atoms may include hydrocarbon groups, such as a nonyl group, a decyl group, a dodecyl group, a hexadecyl group, an octadecyl group, an eicosyl group, etc.; groups derived from olefin polymers (for example, polyethylene, polypropylene, polybutene, etc.); and the like.
  • the alkyl group having 9 to 20 carbon atoms may be any of a linear hydrocarbon group and a branched hydrocarbon group.
  • R 1 and R 2 are each actually a linear hydrocarbon group.
  • R 1 and R 2 are each preferably an alkyl group having 9 to 18 carbon atoms.
  • substituted hydroxy aromatic carboxylic acid ester derivative represented by the foregoing general formula (I) include (hexadecylsalicylic acid) hexadecylphenyl ester, (tetradecylsalicylic acid) tetradecylphenyl ester, (dodecylsalicylic acid) dodecylphenyl ester, (decylsalicyclic acid) decylphenyl ester, (nonylsalicyclic acid) nonylphenyl ester, (hexadecylsalicylic acid) nonylphenyl ester, a (mixed C 11 to C 15 ) alkylsalicylic acid (mixed C 11 to C 15 )alkylphenyl ester, a (mixed C 11 to C 15 )alkylsalicylic acid hexadecylphenyl ester, a (mixed C 11 to
  • substituted hydroxy aromatic carboxylic acid ester derivative represented by the foregoing general formula (II) include (hexadecylsalicylic acid) hexadecylhydroxylphenyl ester, (tetradecylsalicylic acid) tetradecylhydroxyphenyl ester, (dodecylsalicylic acid) dodecylhydroxyphenyl ester, (decylsalicyclic acid) decylhydroxyphenyl ester, (nonylsalicylic acid) nonylhydroxyphenyl ester, (hexadecylsalicylic acid) nonylhydroxyphenyl ester, a (mixed C 11 to C 15 )alkylsalicylic acid hexadecylhydroxyphenyl ester, a (mixed C 11 to C 15 )alkylsalicylic acid dodecylhydroxyphenyl ester, a (mixed C 11
  • the substituted hydroxy aromatic carboxylic acid ester derivative (A) may be a mixture of plural carboxylic acid ester derivatives.
  • the substituted hydroxy aromatic carboxylic acid ester derivative represented by the general formula (I) or (II) is contained in an amount of 60% or more on the basis of a total amount of the mixture of plural carboxylic acid ester derivatives.
  • the amount of the substituted hydroxy aromatic carboxylic acid ester derivative represented by the general formula (I) or (II) is more preferably 65% or more and 100% or less on the basis of a total amount of the mixture of plural carboxylic acid ester derivatives.
  • the amount of the substituted hydroxy aromatic carboxylic acid ester derivative represented by the general formula (I) or (II) is still more preferably 70% or more and 100% or less on the basis of a total amount of the mixture of plural carboxylic acid ester derivatives.
  • the substituted hydroxy aromatic carboxylic acid ester derivative represented by each of the general formulae (I) and (II) is useful as an ash-free detergent, and furthermore, when it is used in combination of an ash-free detergent-dispersant, a lubricating oil composition having excellent high-temperature stability and high-temperature detergency and having a microparticle dispersing action can be formed.
  • the substituted hydroxy aromatic carboxylic acid ester derivative (A) is blended in an amount of preferably 0.01 mass% or more and 10 mass% or less, more preferably 0.1 mass% or more and 8 mass% or less, still more preferably 1 mass% or more and 7 mass% or less, and especially preferably 2 mass% or more and 6 mass% or less on the basis of a total amount of the composition.
  • heterocyclic compound which is used in the present invention is represented by the following general formula (III) or (IV). or
  • R 3 represents a linear or branched alkyl group having 7 to 17 carbon atoms; and n is 6 to 18.
  • the alkyl group is constituted of, for example, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, or 17 carbon atoms.
  • n is preferably 6, 8, 10, 12, 14, 16, or 18.
  • each R 4 is independently a group selected from a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a -COR 5 group, and an -OR 6 group;
  • R 5 is an alkyl group having 1 to 17 carbon atoms;
  • R 6 is an alkyl group having 1 to 18 carbon atoms.
  • R 4 is preferably a hydrogen atom or a methyl group, and R 4 is more preferably a hydrogen atom. That is, the general formula of the more preferred heterocyclic compound (B) is as follows.
  • the heterocyclic compound may be produced by a well-known method.
  • a hindered amine represented by the following formula is preferred as the compound represented by the general formula (IV) wherein R 4 is a methyl group.
  • a hindered amine represented by the following formula is preferred as the compound represented by the general formula (III) or (IV) wherein R 4 is a hydrogen atom. or
  • the heterocyclic compound (B) is blended in an amount of preferably 0.01 mass% or more and 5 mass% or less, more preferably 0.05 mass% or more and 3 mass% or less, and still more preferably 0.1 mass% or more and 2 mass% or less on the basis of a total amount of the composition.
  • the lubricating oil composition of the present invention has the aforementioned constitution, and the phosphorus content and the sulfated ash content on the basis of a total amount of the composition are required such that the phosphorus content is 0.06 mass% or less on the basis of a total amount of the composition; and that the sulfated ash content is 1.2 mass% or less on the basis of a total amount of the composition.
  • the phosphorus content in the composition is more than 0.06 mass% on the basis of a total amount of the composition, a poisoning action of active sites of a three-way catalyst cannot be suppressed, and an effect for prolonging the catalyst service life is not obtained.
  • the sulfated ash content is more than 1.2 mass% on the basis of a total amount of the composition, an ash originated from metallic components is liable to deposit on DPF, and an effect for prolonging the service life of the DPF is not obtained.
  • the phosphorus content is based on JIS-5S-38-92; and that the sulfated ash content is based on JIS K2272.
  • the phosphorus content in the lubricating oil composition is 0.06 mass% or less on the basis of a total amount of the composition, and the sulfated ash content is 0.5 mass% or less on the basis of a total amount of the composition, a poisoning action of active sites of a three-way catalyst can be suppressed, and the catalyst service life can be prolonged.
  • detergency required as the lubricating oil composition for internal combustion engines is obtained, deposition of an ash originated from metallic components on DPF can be suppressed, and an effect for prolonging the service life of the DPF is obtained.
  • the phosphorus content in the lubricating oil composition is 0.06 mass% or less on the basis of a total amount of the composition, and the sulfated ash content is 0.3 mass% or less on the basis of a total amount of the composition, a poisoning action of active sites of a three-way catalyst can be suppressed, and the catalyst service life can be prolonged.
  • high detergency as the lubricating oil composition for internal combustion engines is obtained, deposition of an ash originated from metallic components on DPF can be more suppressed, and the service life of the DPF can be more prolonged.
  • the phosphorus content in the lubricating oil composition is 0.03 mass% or less, and the sulfated ash content is 0.5 mass% or less on the basis of a total amount of the composition, a poisoning action of active sites of a three-way catalyst can be sufficiently suppressed, and the catalyst service life can be more prolonged.
  • detergency required as the lubricating oil composition for internal combustion engines is obtained, deposition of an ash originated from metallic components on DPF can be suppressed, and an effect for prolonging the service life of the DPF is obtained.
  • the phosphorus content in the lubricating oil composition is 0.03 mass% or less on the basis of a total amount of the composition, and the sulfated ash content is 0.3 mass% or less on the basis of a total amount of the composition, a poisoning action of active sites of a three-way catalyst can be sufficiently suppressed, and the catalyst service life can be more prolonged.
  • high detergency as the lubricating oil composition for internal combustion engines is obtained, deposition of an ash originated from metallic components on DPF can be more suppressed, and the service life of the DPF can be more prolonged.
  • the phosphorus content can be adjusted by a blending amount of a phosphorus-based ant-wear agent.
  • a phosphorus-based ant-wear agent include phosphoric acid ester-based compounds and thiophosphoric acid ester-based compounds. Above all, phosphorous acid esters, alkyl hydrogenphosphites, phosphoric acid ester amine salts, and the like are preferred. In the present invention, zinc dithiophosphate (ZnDTP) is especially preferred.
  • the lubricating oil composition of the present invention may be blended with conventionally known additives so long as the effects thereof are not impaired.
  • the additive include a dispersant, an antioxidant, a metallic detergent, a viscosity index improver, a pour point depressant, an anti-wear agent, an extreme pressure agent, a metal deactivator, a rust preventive, a defoaming agent, and the like. It is preferred that the lubricating oil composition of the present invention contains at least one of an antioxidant and a dispersant.
  • a metal-free ash-free dispersant is preferably used.
  • a boronated imide-based dispersant and optionally, a non-boronated imide-based dispersant may be used.
  • the non-boronated imide-based dispersant is one generally called an imide-based dispersant.
  • a polybutenylsuccinimide is suitably used. Examples of the polybutenylsuccinimide include compounds represented by the following formulae (1) and (2).
  • PIB represents a polybutenyl group
  • its number average molecular weight is typically 900 or more and 3,500 or less, and preferably 1,000 or more and 2,000 or less. So long as the number average molecular weight is 900 or more, there is no concern that the dispersibility is deteriorated, whereas so long as it is 3,500 or less, there is no concern that the storage stability is deteriorated.
  • n is typically an integer of 1 to 5, and more preferably an integer of 2 to 4.
  • a method of producing the aforementioned polybutenylsuccinimide is not particularly limited, and the polybutenyl succinic acid imide may be produced by a known method.
  • the polybutenyl succinic acid imide may be obtained by allowing polybutenyl succinic acid which is obtained through reaction of polybutene with maleic anhydride at 100°C or higher and 200°C or lower, to react with a polyamine, such as diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, etc.
  • the boronated imide-based dispersant it is preferred to use a boronated polybutenylsuccinimide obtained by allowing a boron compound to act on the non-boronated imide-based dispersant exemplified by the foregoing general formula (1) or (2).
  • Examples of the boron compound include boric acid, a boric acid salt, a boric acid ester, and the like.
  • Examples of the boric acid include orthoboric acid, metaboric acid, paraboric acid, and the like.
  • suitable examples of the boric acid salt include ammonium salts and the like, for example, ammonium borates, such as ammonium metaborate, ammonium tetraborate, ammonium pentaborate, ammonium octaborate, etc.
  • boric acid ester examples include esters between boric acid and an alkyl alcohol (desirably having 1 to 6 carbon atoms), for example, monomethyl borate, dimethyl borate, trimethyl borate, monoethyl borate, diethyl borate, triethyl borate, monopropyl borate, dipropyl borate, tripropyl borate, monobutyl borate, dibutyl borate, tributyl borate, etc.
  • a mass ratio of a boron content B and a nitrogen content N, B/N, of the boronated polybutenylsuccinimide is preferably 0.1 to 3, and more preferably 0.2 to 1.
  • a content of each of the boronated succinimide-based dispersant and the non-borated succinimide-based dispersant (imide-based dispersant) is preferably 0.1 mass% or more and 15 mass% or less, and more preferably 0.5 mass% or more and 10 mass% or less. So long as the subject content is 0.1 mass% or more, favorable detergency and dispersibility are obtained, whereas so long as it is 15 mass% or less, effects of detergency and dispersibility commensurate with the content are obtained.
  • the antioxidant is preferably a phosphorus-free antioxidant.
  • examples thereof include a phenol-based antioxidant, an amine-based antioxidant, a molybdenum-amine complex-based antioxidant, a sulfur-based antioxidant, and the like.
  • phenol-based antioxidant examples include 4,4'-methylene bis(2,6-di-t-butylphenol), 4,4'-bis(2,6-di-t-butylphenol), 4,4'-bis(2-methyl-6-t-butylphenol), 2,2'-methylene bis(4-ethyl-6-t-butylphenol), 2,2'-methylene bis(4-methyl-6-t-butylphenol), 4,4'-butylidene bis(3-methyl-6-t-butylphenol), 4,4'-isopropylidene bis(2,6-di-t-butylphenol), 2,2'-methylene bis(4-methyl-6-nonylphenol), 2,2'-isobutylidene bis(4,6-dimethylphenol), 2,2'-methylene bis(4-methyl-6-cyclohexylphenol), 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-ethylphenol, 2,6
  • bisphenol-based antioxidants and ester group-containing phenol-based antioxidants are especially suitable.
  • amine-based antioxidant examples include monoalkyldiphenylamine-based antioxidants, such as monooctyldiphenylamine, monononyldiphenylamine, etc.; dialkyldiphenylamine-based antioxidants, such as 4,4'-dibutyldiphenylamine, 4,4'-dipentyldiphenylamine, 4,4'-dihexyldiphenylamine, 4,4'-diheptyldiphenylamine, 4,4'-dioctyldiphenylamine, 4,4'-dinonyldiphenylamine, etc.; polyalkyldiphenylamine-based antioxidants, such as tetrabutyldiphenylamine, tetrahexyldiphenylamine, tetraoctyldiphenylamine, tetranonyldiphenylamine, etc.; ⁇ -naphthylamine; phenyl- ⁇ -n
  • dialkyldiphenylamine-based antioxidants and naphthylamine-based antioxidants are suitable.
  • molybdenum-amine complex-based antioxidant a complex formed through reaction of a hexavalent molybdenum compound, specifically, molybdenum trioxide and/or molybdic acid, with an amine compound, for example, a compound produced by the production method described in JP 2003-252887A , may be used.
  • a hexavalent molybdenum compound specifically, molybdenum trioxide and/or molybdic acid
  • an amine compound for example, a compound produced by the production method described in JP 2003-252887A
  • the amine compound to be reacted with a hexavalent molybdenum compound is not particularly limited, specifically, examples thereof include a monoamine, a diamine, a polyamine, and an alkanolamine. More particularly there are exemplified alkylamines having an alkyl group with from 1 to 30 carbon atoms (in which the alkyl group may be linear or branched) such as methylamine, ethylamine, dimethylamine, diethylamine, methylethylamine, methylpropylamine, etc.; alkenylamines having an alkenyl group with from 2 to 30 carbon atoms (in which the alkenyl group may be linear or branched) such as ethenylamine, propenylamine, butenylamine, octenylamine, oleylamine, etc.; alkanolamines having an alkanol group with from 1 to 30 carbon atoms (in which the alkanol group may be linear
  • this molybdenum complex may also be produced through the following steps (o), (p), and (q).
  • sulfur-based antioxidant examples include phenothiazine, pentaerythritol-tetrakis-(3-laurylthiopropionate), didodecyl sulfide, dioctadecyl sulfide, didodecyl thiodipropionate, dioctadecyl thiodipropionate, dimyristyl thiodipropionate, dodecyloctadecyl thiodipropionate, 2-mercaptobenzoimidazole, and the like.
  • antioxidants phenol-based antioxidants and amine-based antioxidants are preferred from the viewpoint of reducing metallic components or sulfur components.
  • the aforementioned antioxidants may be used alone or in admixture of two or more thereof. From the viewpoint of an effect of oxidation stability, a mixture of one or more phenol-based antioxidant and one or more amine-based antioxidants is preferred.
  • a blending amount of the antioxidant is preferably in the range of 0.1 mass% or more and 5 mass% or less, and more preferably in the range of 0.1 mass% or more and 3 mass% or less on the basis of a total amount of the composition.
  • a blending amount, as reduced to the molybdenum content, of the molybdenum complex is preferably 10 ppm by mass or more and 1,000 ppm by mass or less, more preferably 30 ppm by mass or more and 800 ppm by mass or less, and still more preferably 50 ppm by mass or more and 500 ppm by mass or less on the basis of a total amount of the composition.
  • an arbitrary alkaline earth metal-based detergent which is used for lubricating oils may be used, and examples thereof include an alkaline earth metal sulfonate, an alkaline earth metal phenate, an alkaline earth metal salicylate, a mixture of two or more selected among these members, and the like.
  • alkaline earth metal sulfonate examples include alkaline earth metal salts of an alkyl aromatic sulfonic acid, which are obtained through sulfonation of an alkyl aromatic compound having a molecular weight of 300 or more and 1, 500 or less, and preferably 400 or more and 700 or less, particularly magnesium salts and/or calcium salts thereof, or the like. Above all, calcium salts are preferably used.
  • alkaline earth metal phenate examples include alkaline earth metal salts of an alkylphenol, an alkylphenol sulfide, or a Mannich reaction product of an alkylphenol, particularly magnesium salts and/or calcium salts thereof, or the like. Above all, calcium salts are especially preferably used.
  • alkaline earth metal salicylate examples include alkaline earth metal salts of an alkylsalicylic acid, particularly magnesium salts and/or calcium salts thereof, or the like. Above all, calcium salts are preferably used.
  • the alkyl group constituting the alkaline earth metal-based detergent is an alkyl group having preferably 4 to 30 carbon atoms, and more preferably 6 to 18 carbon atoms. Such an alkyl group may be linear or branched.
  • the alkyl group may be a primary alkyl group, a secondary alkyl group, or a tertiary alkyl group.
  • the alkaline earth metal sulfonate, alkaline earth metal phenate, and alkaline earth metal salicylate include a neutral alkaline earth metal sulfonate, a neutral alkaline earth metal phenate, and a neutral alkaline earth metal salicylate, which are obtained by reacting the aforementioned alkyl aromatic sulfonic acid, alkylphenol, alkylphenol sulfide, Mannich reaction product of an alkylphenol, or alkylsalicylic acid, or the like directly with an alkaline earth metal oxide or an alkaline earth metal base, such as a hydroxide thereof, etc., the alkaline earth metal being magnesium and/or calcium, or once converting the alkyl aromatic sulfonic acid, alkylphenol, alkylphenol sulfide, Mannich reaction product of an alkylphenol, alkylsalicylic acid, or the like to an alkali metal salt, such as a sodium salt, a potassium salt, etc.,
  • the alkaline earth metal sulfonate, alkaline earth metal phenate, and alkaline earth metal salicylate also include a basic alkaline earth metal sulfonate, a basic alkaline earth metal phenate, and a basic alkaline earth metal salicylate, which are produced by heating the neutral alkaline earth metal sulfonate, neutral alkaline earth metal phenate, and neutral alkaline earth metal salicylate, with an excessive of an alkaline earth metal salt or an alkaline earth metal base in the presence of water; and a overbased alkaline earth metal sulfonate, a overbased alkaline earth metal phenate, and a overbased alkaline earth metal salicylate, which are obtained by reacting the neutral alkaline earth metal sulfonate, neutral alkaline earth metal phenate, and neutral alkaline earth metal salicylate with an alkaline earth metal carbonate or borate in the presence of carbon dioxide.
  • the metallic detergent which is used in the present invention is preferably an alkaline earth metal salicylate or an alkaline earth metal phenate.
  • a overbased salicylate and a overbased phenate are preferred, with overbased calcium phenate being especially preferred.
  • the metallic detergent which is used in the present invention has a total base number of preferably in the range of 10 mgKOH/g or more and 500 mgKOH/g or less, and more preferably in the range of 15 mgKOH/g or more and 450 mgKOH/g or less.
  • the metallic detergent may be used alone or in combination of two or more thereof.
  • the total base number as referred to herein means the total base number according to potentiometric titration (base number-perchloric acid method) to be measured according to 7. "Petroleum Product And Lubricants - Neutralization Number Test Method" in JIS K 2501.
  • a metal ratio of the metallic detergent which is used in the present invention is not particularly limited, in general, one or more metallic detergents having a metal ratio of 20 or less may be used. It is especially desirable that a metallic detergent having a metal ratio of 3 or less, more preferably 1.5 or less, even more preferably 1.2 or less is used as the essential component from the viewpoint of being more excellent in oxidation stability, base number retention and high-temperature detergency and the like.
  • the metal ratio as referred to herein is represented by (number of valences of metal element in metallic detergent) x (metal element content (mol%))/(soap group content (mol%)).
  • the metal element means calcium, magnesium, etc.; and the soap group means a sulfonic acid group, a phenol group, a salicylic acid group, etc.
  • a blending amount of the metallic detergent is preferably in the range of 0 mass% or more and 20 mass% or less, more preferably in the range of 0.01 mass% or more and 20 mass% or less, still more preferably in the range of 0.05 mass% or more and 10 mass% or less, and especially preferably in the range of 0.1 mass% or more and 5 mass% or less on the basis of a total amount of the lubricating oil composition.
  • the blending amount of the metallic detergent is 0.01 mass% or more, performances, such as high-temperature detergency, oxidation stability, maintainability of base number, etc., are liable to be obtained. Meanwhile, so long as the blending amount is 20 mass% or less, the effects commensurate with its addition amount are generally obtained. However, as for an upper limit of the blending amount of the metallic detergent, it is important to make the blending amount low as far as possible in spite of the foregoing range. According to this, the metallic content, i.e., the sulfated ash content, of the lubricating oil composition is reduced, so that deterioration of an exhaust gas cleaner of automobiles can be prevented from occurring.
  • the metallic detergent may be used alone or in combination of two or more thereof so long as it is contained in the aforementioned prescribed amount.
  • overbased calcium salicylate or overbased calcium phenate is especially preferred, and among the ash-free dispersants, the aforementioned polybutenyl succinic acid bisimide is particularly preferred.
  • the total base number of each of the aforementioned overbased calcium salicylate and overbased calcium phenate is preferably in the range of 100 mgKOH/g or more and 500 mgKOH/g or less, and more preferably in the range of 200 mgKOH/g or more and 500 mgKOH/g or less.
  • the viscosity index improver includes, for example, polymethacrylates, dispersant-type polymethacrylates, olefinic copolymers (for example, ethylene-propylene copolymers), dispersant-type olefinic copolymers, styrenic copolymers (for example, styrene-diene copolymers, styrene-isoprene copolymers), etc.
  • the blending amount of the viscosity index improver may be from 0.5% by mass to 15% by mass, preferably from 1 % by mass to 10% by mass based on the total amount of the composition, from the viewpoint of the blending effect.
  • the pour point depressant includes, for example, polymethacrylates having a mass average molecular weight of about 5,000 or more and about 50,000 or less, and the like.
  • a blending amount of the pour point depressant is preferably in the range of 0.1 mass% or more and 2 mass% or less, and more preferably in the range of 0.1 mass% or more and 1 mass% or less on the basis of a total amount of the lubricating oil composition from the standpoint of its blending effect.
  • Examples of the anti-wear agent or the extreme pressure agent include sulfur-containing compounds such as zinc dithiophosphate, zinc phosphate, zinc dithiocarbamate, molybdenum dithiocarbamate, molybdenum dithiophosphate, disulfides, olefin sulfides, sulfurized oils and fats, sulfurized esters, thiocarbonates, thiocarbamates, and polysulfides; phosphorus-containing compounds such as phosphorous acid esters, phosphoric acid esters, phosphonic acid esters, and amine salts or metal salts of those compounds; sulfur- and phosphorus-containing anti-wear agents, such as thiophosphorous acid esters, thiophosphorous acid esters, thiophosphonic acid esters, and amine salts or metal salts of those compounds.
  • sulfur- and phosphorus-containing anti-wear agents such as thiophosphorous acid esters, thiophosphorous acid esters, thiophosphonic acid esters, and amine salt
  • the blending amount of the anti-wearing or the extreme pressure agent is preferably in the range of 0 mass% or more and 3 mass% or less, and more preferably in the range of 0.01 mass% or more and 2 mass% or less on the based on the total amount of the lubricating oil composition.
  • the lubricating oil composition of the present invention may further contain a friction modifier, an anti-wear agent, or an extreme pressure agent in accordance with need.
  • this friction modifier refers to a compound other than the polar group-containing compound that is an essential component of the present invention.
  • a blending amount of the friction modifier is preferably in the range of 0.01 mass% or more and 2 mass% or less, and more preferably in the range of 0.01 mass% or more and 1 mass% or less on the basis of a total amount of the lubricating oil composition.
  • the metal deactivator includes, for example, benzotriazole compounds, tolyltriazole compounds, thiadiazole compounds, imidazole compounds, etc.
  • the rust inhibitor includes, for example, petroleum sulfonate, alkylbenzene sulfonates, dinonylnaphthalene sulfonates, alkenyl succinic acid esters, a polyhydric alcohol ester, etc.
  • the defoaming agent includes for example, silicone oil, fluorosilicone oil, fluoroalkyl ether, etc.
  • the lubricating oil composition of the present invention may be preferably used as a lubricating oil for internal combustion engines, such as gasoline engines, diesel engines, gas engines, etc., for two-wheeled vehicles, four-wheeled vehicles, power generation facilities, water vehicles, etc.
  • internal combustion engines such as gasoline engines, diesel engines, gas engines, etc.
  • the lubricating oil composition of the present invention can be suitably used for lubrication of internal combustion engines equipped with an exhaust gas cleaner.
  • the production method of a lubricating oil composition is a method for producing a lubricating oil composition containing blending a base oil, (A) a substituted hydroxy aromatic carboxylic acid ester derivative represented by at least one of the general formula (I) and the general formula (II), and (B) a heterocyclic compound represented by the formula (III) or (IV), thereby producing a lubricating oil composition having a phosphorus content of 0.06 mass% or less on the basis of a total amount of the composition and a sulfated ash content of 1.2 mass% or less on the basis of a total amount of the composition.
  • each of x and y is an integer satisfying (1 ⁇ x ⁇ 3) and (1 ⁇ y ⁇ 3), respectively; each of R 1 and R 2 represents an alkyl group having 9 to 20 carbon atoms and may be the same as or different from each other; and in the case of (2 ⁇ x ⁇ 3) and (2 ⁇ y ⁇ 3), plural R 1 s may be the same as or different from each other and plural R 2 s may be the same as or different from each other.
  • each of m, n, o, and p is an integer satisfying (1 ⁇ m ⁇ 2), (0 ⁇ n ⁇ 2), (2 ⁇ (m + n) ⁇ 4), (1 ⁇ o ⁇ 3), and (1 ⁇ p ⁇ 3), respectively; each of R 1 and R 2 represents an alkyl group having 9 to 20 carbon atoms and may be the same as or different from each other; and in the case of (2 ⁇ o ⁇ 3) and (2 ⁇ p ⁇ 3), plural R 1 s may be the same as or different from each other and plural R 2 s may be the same as or different from each other. or
  • R 3 represents a linear or branched alkyl group having 7 to 17 carbon atoms; n is 6 to 18; in the case where a plurality of R 4 s are present, each R 4 is independently a group selected from a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a -COR 5 group, and an -OR 6 group; R 5 is an alkyl group having 1 to 17 carbon atoms; and R 6 is an alkyl group having 1 to 18 carbon atoms.
  • a lubricating oil composition capable of maintaining high-temperature detergency and acid neutralizing properties, even when amounts of a phosphorus component-containing additive and a metallic detergent are reduced.
  • the blending amounts of the component (A) and the component (B) in the base oil are those described above for the suitable contents in the lubricating oil composition.
  • the aforementioned additives may be added in the suitable contents as described above, as the need arises.
  • the temperature was dropped to 80°C, the resultant was transferred into a 2-liter flask, 120 g of xylene was added, and the contents were stirred such that the system became uniform. Furthermore, 250 g of 20 weight% sulfuric acid was added over 30 minutes, followed by undergoing reaction for 1 hour. This reaction solution was washed with water to perform phase separation, and thereafter, filtration was performed, followed by distilling away the xylene. A yield of the resulting reaction product was 312 g.
  • Lubricating oil compositions were prepared by blending additives in a base oil in a blending formulation shown in Table 1. Properties and performances of each of the resulting methods. The results are shown in Table 1.
  • Lubricating oil compositions for internal combustion engines were prepared by blending additives in a base oil in a blending formulation shown in Table 2. Properties and performances of each of the resulting lubricating oil compositions were evaluated by the aforementioned methods. The results are shown in Table 2.
  • Lubricating oil compositions for internal combustion engines were prepared by blending additives in a base oil in a blending formulation shown in Table 3. Properties and performances of each of the resulting lubricating oil compositions were evaluated by the aforementioned methods. The results are shown in Table 3.
  • Lubricating oil compositions for internal combustion engines were prepared by blending additives in a base oil in a blending formulation shown in Table 4. Properties and performances of each of the resulting lubricating oil compositions were evaluated by the aforementioned methods. The results are shown in Table 4.

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CN105441168A (zh) * 2015-11-30 2016-03-30 蚌埠市华科机电有限责任公司 一种摩擦改进型润滑油
KR102813707B1 (ko) * 2016-01-22 2025-05-28 셰브런 오로나이트 컴퍼니 엘엘씨 올레핀 공중합체 분산제-유형 점도 향상제 및 아민 화합물의 혼합물을 함유하는 시너지 윤활유 조성물
JP6711512B2 (ja) * 2016-02-24 2020-06-17 出光興産株式会社 潤滑油組成物、及び当該潤滑油組成物の製造方法
JP7721268B2 (ja) * 2018-03-14 2025-08-12 出光興産株式会社 潤滑油組成物
JP7429509B2 (ja) * 2019-09-17 2024-02-08 出光興産株式会社 潤滑油組成物
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CN105229128A (zh) 2016-01-06
US9850446B2 (en) 2017-12-26
JPWO2014189057A1 (ja) 2017-02-23
CN105229128B (zh) 2018-07-06
WO2014189057A1 (ja) 2014-11-27
US20160115419A1 (en) 2016-04-28
JP6389458B2 (ja) 2018-09-12

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